33 Jennings Lane
Windham, Connecticut 06280
- Beds
- 4
- Baths
- 2
- SqFt
- 2,040
- Acres
- 2.00
- Year Built
- 1967
- Property Type
- Single Family

Matt Caiola
Luxury Real Estate Advisor
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About This Home
Completely renovated from top to bottom, this move-in ready raised ranch sits on 2 private acres and offers the perfect blend of modern farmhouse design, quality craftsmanship, and today's most desirable upgrades. With approximately 2,000 square feet of beautifully finished living space, this home features 4 bedrooms, plus an office/recreation room, 2 full bathrooms, and a finished walkout lower level with a spacious entertainment room. The heart of the home is the stunning designer kitchen, thoughtfully remodeled with quartz countertops, a timeless tiled backsplash, brand-new stainless-steel appliances, and an expansive peninsula offering additional seating, prep space, and effortless entertaining. A dedicated coffee bar adds both charm and functionality, while the abundance of countertop space and cabinetry provides exceptional storage. The kitchen flows seamlessly into the dining area, where French doors open to the insulated four-season porch, creating the perfect place to enjoy your morning coffee while overlooking the private backyard. Large windows throughout the home fill every room with an abundance of natural light. Just off the kitchen, you'll find a beautifully renovated mudroom that connects the home to the attached two-car garage, offering a stylish and practical transition between the garage and the main living area.
Key Facts
- City/Town
- Windham
- Neighborhood
- N/A
- Property / Style
- Single Family · Raised Ranch
- Year Built
- 1967
- Days on Market
- 16 days
- Beds
- 4
- Baths
- 2 full
- Living Area
- 2,040 sq ft
- Lot Size
- 2.00 acres
- Garage / Parking
- 2 garage
- Property Taxes
- $5,480 / Annually
Market Snapshot
The Windham Market
Single Family · trailing 12 months
Active Listings
13
40 under contract
Median List Price
$299,900
13 active listings
Median Closed Price
$271,000
166 sales
Median Days on Market
19
13 active listings
Median $ / Sq Ft
$203
13 active listings
Sale-to-List Ratio
100.7%
166 sales
How this home compares
List Price
$399,900
vs $299,900 median
33.3% above median
Price / Sq Ft
$196
vs $203 median
In line with median
Days on Market
16 days
vs 19 days median
3 days fresher than median
Based on 13 active and 166 closed sales (trailing 12 mo) of single family in Windham. Source: SmartMLS · As of July 28, 2026.
Location
33 Jennings Lane, Windham, Connecticut
Estimate Your Payment
Estimated Monthly Payment
Rates: Freddie Mac PMMS via FRED · Updated Jul 23, 2026per month
- Principal & Interest$2,039
- Property Taxes$457
- Insurance$133
- HOA$0
Estimates only. Actual rates, taxes, insurance, and HOA fees vary. Consult a lender for current rates.
Location
- City/Town
- Windham
- Neighborhood
- N/A
- County
- Windham
Residence
- Property Type
- Single Family
- Style
- Raised Ranch
- Year Built
- 1967
- New Construction
- No/Resale
- Living Area
- 2,040 sq ft
- Below Grade
- 1,000 sq ft
Schools
- Elementary
- Per Board of Ed
- High
- Windham
Interior
- Heating
- Heat Pump
- Heat Fuel
- Electric
- Cooling
- Central AirSplit System
- Fireplaces
- 1
- Laundry
- Lower Level
- Appliances
- Electric RangeRange HoodRefrigeratorDishwasherWasherDryer
- Basement
- FullFully Finished
- In-Law Apartment
- No
- Additional Rooms
- Bonus RoomBreezeway
Exterior & Lot
- Lot Size
- 2.00 acres
- Zoning
- R3
- Garage / Parking
- 2 garage spacesAttached Garage
- Waterfront Details
- Not Applicable
- Water Source
- Private Well
- Sewer
- Septic
- Construction
- Vinyl Siding
- Color
- White
- Roof
- Asphalt Shingle
- Foundation
- Concrete
- Exterior Features
- Deck
- Lot Description
- Level LotClearedProfessionally Landscaped
Listing & Financials
- Property Taxes
- $5,480 / Annually
- Days on Market
- 16
- MLS #
- 24190853
- MLS Status
- Under Contract
- Financing
- FHA,VA,CHFA
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This information is believed to be accurate, but without warranty.
The IDX display contains information sourced from SmartMLS, Inc. as of 7/28/2026. This information is provided for consumers' personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing or leasing. Data is deemed reliable but is not guaranteed accurate by the MLS, the listing broker, the listing agent, or Matt Caiola. Buyers and tenants should independently verify all information that matters to their decision.
Map locations may be approximate. Any offer of compensation, if applicable, is made only to participants of the MLS where the listing is filed. ©2026 Smart MLS, Inc. All rights reserved.
Data last updated on 7/28/2026 at 7:45 AM UTC.